>I was 15 and horny as fuk
>was at a public pool
>fooling around being a brat w/ my mom
>trying to play-drown her.
>I get the idea to pick her up and take her to the deeper end.
>I'm taller than her, she's petite.
>she doesn't trust me in the deep end
>she's clinging for dear life onto me
>she cant reach the floor with her feet
>can tread water, but she's too scared to let me go
>shes thinking im gonna do something.
>I can feel her on my back with her legs wrapped around me
>primal arousal feeling goes through me feeling her cling to me sorta sexually
>try not to touch my raging boner on her legs/feet
>have her to myself in the deep end for a few minutes, she relaxes
>she now is floating on her back with me supporting her from her neck/shoulders
>our cheeks are together
>im looking down her massive cleavage
>v.close and intimate moment having her like that
>cheeks almost caressing each other
>my boner rages
>I take her out of deep end
>as she goes down to touch the floor with her feet my boner tip nudges into her asscheeks
>extremely awkward moment, we dont say anything
>we know exactly what happened, its still nudged in her, i feel like im gonna bust.
>she pulls away like nothing happened
>we dont speak to each other for an hour
>hour later, no more awkwardness, she's like it never happened
>get home, jerk off a huge load to the feeling of her ass-cheeks nestled around my cock.
>eventually find /ss/ and shit bricks

I was a cute kid, and she was a friend of a friend's neighbor. Said neighbor threw a party and I was invited. Me and friend had a sort of loose concept of a band going on, and we weaseled our way into playing. We were decent, I was the guitarist/singer so I had girls talking to me after playing. She immediately struck me as someone VERY attractive. She was laid back, chill, had short choppy hair, was slightly taller than me and very skinny (Later found out she was anorexic. She's put on some pounds now.) She also played the drums, kind of like >>53052152. She told me I was very talented and that I probably have to beat off girls with a stick when I go into public. She wanted to take a walk with me, so we did. When we were alone outside we talked for a while until happenstance made our eyes meet. I don't know what came over me, but her big brown eyes and the expression on her face combined with the silence...it was just too inviting. I kissed her passionately. It seemed like it lasted forever. When we paused to stare into each others eyes again, she told me I was amazing and that we should head back to her car. I was so fucking nervous I felt like I was going to throw up. The entire situation seemed too good to be true. When we got inside she expressed how wet she was while she touched my chest. We kissed more, and we removed each other's clothes. I had slight trouble with her bra, and I think she knew it. When she pulled down my boxers she was surprised at how big I was. She told me I didn't need to do the whole emotional musician shtick if I was packing heat like that. The most embarrassing part was I didn't know where to stick it. That's when she knew. She asked me if I've ever done anything like that before. I of course, lied. I said I couldn't see. She guided me in and that's pretty much it. She was 18, I was 16. I tried to see her at school but the whole social stigma of being with a younger guy really got to her. Plus her friends were assholes. Mostly guys her age that wanted to fuck her and were jealous that a kid got in her pants before their neckbearded hipster ass did. I'm still friends with her on FB but I haven't talked to her in years.

The whole idea of being with someone older has stuck with me, though. It's like /ss/ in porn. The comforting voice, the maternal guidance, the biddies all that shit. Right now I'm fooling around with a milf at my workplace. Same type of girl, just older.